(2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal

Base Information

• Chemical Name: (2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal
• CAS No.: 960012-26-4
• Molecular Formula: C₃₅H₆₆O₅Si₂
• Molecular Weight: 623.077

Synonyms:(2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal

Chemical Property of (2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal

There total 10 articles about (2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2R,4S)-5-benzyloxy-2,4-dimethylpentanal → (2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal (960012-26-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

2.2: 1.08 h / -78 - 0 °C / Inert atmosphere

3.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II) / isopropyl alcohol / 5 h / 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

5.1: Wilkinson's catalyst; hydrogen / benzene / 3000.3 Torr

6.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

7.1: hydrogen / ethanol

8.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Inert atmosphere

With 2,6-dimethylpyridine; Wilkinson's catalyst; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; tetrapropylammonium perruthennate; hydrogen; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; isopropyl alcohol; benzene; 1.1: Shioiri alkynylation / 1.2: Shioiri alkynylation;

DOI:10.1002/ejoc.201100244

Reference yield:

(2R,4S)-5-(benzyloxy)-2,4-dimethylpentan-1-ol (169105-67-3) → (2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal (960012-26-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: pyridine; Dess-Martin periodane / dichloromethane / Inert atmosphere

2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

3.2: 1.08 h / -78 - 0 °C / Inert atmosphere

4.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II) / isopropyl alcohol / 5 h / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

6.1: Wilkinson's catalyst; hydrogen / benzene / 3000.3 Torr

7.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

8.1: hydrogen / ethanol

9.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; Wilkinson's catalyst; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; tetrapropylammonium perruthennate; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; isopropyl alcohol; benzene; 1.1: Dess-Martin oxidation / 2.1: Shioiri alkynylation / 2.2: Shioiri alkynylation;

DOI:10.1002/ejoc.201100244

Reference yield:

1-((2R,4S)-5-benzyloxy-2,4-dimethylpentyloxymethyl)-4-methoxybenzene → (2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal (960012-26-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: ammonium cerium (IV) nitrate; water / acetonitrile / 0 °C / Inert atmosphere

2.1: pyridine; Dess-Martin periodane / dichloromethane / Inert atmosphere

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

4.2: 1.08 h / -78 - 0 °C / Inert atmosphere

5.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II) / isopropyl alcohol / 5 h / 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

7.1: Wilkinson's catalyst; hydrogen / benzene / 3000.3 Torr

8.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

9.1: hydrogen / ethanol

10.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; Wilkinson's catalyst; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; ammonium cerium (IV) nitrate; tetrapropylammonium perruthennate; water; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; isopropyl alcohol; acetonitrile; benzene; 2.1: Dess-Martin oxidation / 3.1: Shioiri alkynylation / 3.2: Shioiri alkynylation;

DOI:10.1002/ejoc.201100244

upstream raw materials:

({[(2S,4R)-2,4-dimethylhex-5-yn-1-yl]oxy}methyl)benzene

(2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one

[2S,4R]-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol

(2R,4S)-5-(benzyloxy)-2,4-dimethylpentan-1-ol

Downstream raw materials:

(3S,4R,5S,7S,10R,11R,12S,13S)-10,14-bis(tert-butyldimethylsilanyloxy)-12-(4-methoxybenzyloxy)-3,5,7,11,13-pentamethyltetradec-1-yn-4-ol

(5R,6S,8S,11R)-5-((S,Z)-4-iodobut-3-en-2-yl)-11-((2R,3S,4S,Z)-3-(4-methoxybenzyloxy)-4-methylocta-5,7-dien-2-yl)-2,2,3,3,6,8,13,13,14,14-decamethyl-4,12-dioxa-3,13-disilapentadecane

(5R,6S,8S,11R,12R,13S,14S)-11-(tert-butyldimethylsilyloxy)-5-[(S)-4-iodobut-3-yn-2-yl]-13-[(4-methoxybenzyl)oxy]-2,2,3,3,6,8,12,14,17,17,18,18-dodecamethyl-4,16-dioxa-3,17-disilanonadecane

(5R,6S,8S,11R,12R,13S,14S)-11-(tert-butyldimethylsilyloxy)-5-[(S,Z)-4-iodobut-3-en-2-yl]-13-[(4-methoxybenzyl)oxy]-2,2,3,3,6,8,12,14,17,17,18,18-dodecamethyl-4,16-dioxa-3,17-disilanonadecane

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